Vat dyestuff of the anthanthrone series



Patented June 1, 1943 T I V UNITED STATES PATENT orrice Werner Zerwecliand Rudolf Miiller, Frankforton-the-Main-Fechenheini, and Kurt Bahr, Lev erkusen I. G. Werk, Germany, assignors to General Aniline & Film Corporation, New York, N. Y.. a corporation of Delaware No Drawing. Application June 14, 1940, Serial No. 340,546. In Germany June 27, 1939 3 Claims. (Cl. 260359) Our present invention relates to vat dyestuffs The course of the reaction is surprising, since of the anthanthrone series, more particularly to it could not be foreseen that in this way conthose of the general formula: densat'ion products would .be obtained which contain two different aminoanthraquinone radicles 5 in the molecule. It would have been expected that mixtures of two symmetrical condensation products as described in U. S. Patent 1,880,440 or also mixtures thereof with asymmetrical condensation products would be formed. Contrary thereto compounds of the aforesaid formula are obtained in a uniform or practically uniform reaction and in good purity.

g The new compounds thus obtained are valuable vat dyestufis, dyeing vegetable fibers mostly in wherein one of R and R1 stands for the anthra- 1 blue to grey shades. The dyestuffs are distinquinone radicle and the other for the radicle of gui'shed by their ability to be absorbed equally an aroylaminoanthraquinone. on the fiber, even onmlxed fabrics. The dyeings U. S. Patent 1,880,440 describes and claims vat thus obtained exhibit excellent fastness properyestuffs of the anthanthrone series obtained by ties and surpass the dyeings obtained by means Condensing a halogenated anthanthrone with an of the dyestuffs prepared according to U. S. Patquinone or a derivative or substient No. 1,880,440 by better fastness to boiling with t on pr d thereof n the p n e of n ent alkaline solutions, bucking, mercerising and ironfor combining with acid and a small quantity in of a catalytically acting substance, such as cop- In order to further illustrate our invention the per or a copper compound or copper salt. By following example is given, the parts being by this means in the molecule of the halogen-anweight and all temperatures in degrees centithanthrones or their derivatives the halogen atgrade,

oms are wholly or in part replaced by the rad- Example icles of aminoanthraquinones or their derivatives. 4.64 parts of 2.7-dibromo-anthanthrone are According to our present invention condensaintroduced at about 200 into a mixture of 200 tion products of the anthanthrone series which parts of naphthalene or nitrobenzene, 3.42 parts contain the radicles of two different aminoanof 1-benzoylamino-4-aminoanthraquinone, 2.23

thr'aq'uinones in the molecule are obtained by p ts f m a hraqu n parts of soacting with mixtures of equimolecular amounts dium carbonate, 8 parts of sodium acetate and of an aminoanthraquinone and a mohoaroylated 0.6 part of cuprous chloride. The mixture is diaminoanthraquinone on halogenanthanthrones heated for about 4 to 6 hours at 200 to 210. containing two halogen atoms in the molecule. Thereupon it is diluted with solvent naphtha or The condensation is performed in the usual manther appropriate 1vem; a d filter d fi while 6 y heatin t e co p n in -boi hot. After removal of the solvent by means of solvents with the addition of acid-binding agents 'tffyl alcohol t residue formed is freed from such as for example sodium or pot s m organic impurities by means of dilute hydrochlorbon'ate or sodium ace t and n thepresenc 0f ric acid. Then the new dyestuff thus obtained of copper or a copper compound nc d g DDe '45 t for ula;

salts.

is filtered off, washed with water and dried. It crystallizes from high-boiling solvents such as for example chloronaphthalene in blue needles, soluble in concentrated sulfuric acid with an olive green color, and dyes cotton from a dark red vat bluish-grey shades of excellent fastness properties.

When replacing the aforesaid l-benzoylamino 4 aminoanthraquinone by the same wherein one of R and R1 stands for the anthraquinone radicle and the other for the radicle of a benzoylamino-anthraquinone, which dyestuffs dye the vegetable fibers mostly blue to grey shades of excellent fastness properties, which dyestuffs are distinguished by their ability to be absorbed equally on the fiber, even on mixed fabrics.

2. A vat dyestuff of the anthanthrone series of amount of 1-benzoylamino-5-aminoanthraquithe formula? none the formed isomeric dyestufi of the formula:

dissolves in concentrated sulfuric acid'with a which dyestufi is soluble in concentrated sulfuric acid with an olive green color, and dyes cotton from a dark red vat bluish-grey shades of exyellowish olive color and dyes cotton from a; 45 cellent fastness properties.

r 3; A vat dyestuff of the anthanthrone series of the formula:

dark red vat bluish grey shades of a somewhat more reddish tint.

We claim:

1. Vat dyestuffs of the anthanthrone series 60 of the formula UQQ whichdyestufi is soluble in concentrated sulfuric acid with a yellowish olive color anddyes cotton from a dark red vat bluish grey shades of a '1 somewhat reddish tint.

WERNER ZERWECK. RUDOLE Mt'ILLER. KURT BAHR. 

